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Holiday Vacation with Pools in Wintergreen, VA

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    Travellers to Wintergreen are booking October dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 48
    5 of 5 stars (7) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    1 / 27
    5 of 5 stars (4) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    1 / 13
    5 of 5 stars (17) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 46
    5 of 5 stars (15) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Skiing: Property Is...
    • Satellite TV
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    North Ridge Condos at Wintergreen Resort, VA - top of the mountain near Wintergarden and Devils Knob Golf/Tennis. WiFi available along with TV in each bedroom and den. Discount passes available for limited sporting activities. Walking distance to Wintergarden/ Devil's Knob Golf Course/Tennis Courts... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 4 weeks ago
    Condo unit was clean and well stocked with towels, bedding, and kitchen items. We did not plan on cooking in the condo, but kitchen was well stocked with items you would need if...
    4 of 5 stars Reviewed 9 February 2016
    The condo was perfect for our group--plenty of space for us all with all the amenities you could ask for. It was on the bus line to the ski lodge which made getting around very...
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    1 / 26
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
    • Mountain Views
    • Hot Tub
    • DVD Player
    • Shared Indoor Pool
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Walk to Golf Clubhouse, Spa, Pool, Membership Access to all Facilities Sit on the Balcony and Enjoy the Gorgeous Golf /Fairway View. Membership Passes We have two units - one on the first floor one one the second floor. Do you have a large party, but would enjoy so space... this may be your... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 30 December 2015
    Beautiful apartment in the heart of Wintergreen resorts with close access to the aquatics, gym and spa club house and sitting practically right on the golf course. The members...
    5 of 5 stars Reviewed 24 October 2015
    October in the Shenandoah, where else would you want to be? Situated on the Devil's Knob Golf course in the Wintergreen Resort, this condo is outstanding for it's coziness...
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    1 / 5
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Internet Access
    • Washer
    • Satellite TV
    • Parking
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Revel in this condominium atop the Blue Ridge at award-winning Wintergreen Resort, 45 minutes southwest of Charlottesville, two hours and 45 minutes from Washington. The unit is available for weekly/weekend rentals at super discount rates from the owner. You'll have most amenities of the resort at... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 8 December 2014
    very nice accomidations. We had plenty to do around us and enjoyed our time there. Condo was nicely furnished.
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    1 / 23
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    We built our log cabin in 2005 just after we fell in love with the Wintergreen community. Much like you we searched for a place to stay at Wintergreen and after such a great experieince we decided to come back and look for a lot to build on. For us Wintergreen was perfect for a young family living... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 1 week ago
    Our family of three humans and one dog, thoroughly enjoyed our time at the cabin. It was clean, spacious, comfortable, and located in a quiet residential neighborhood. The...
    5 of 5 stars Reviewed 2 June 2016
    The house was very clean. The bedroom, bathrooms, were in great condition. All the appliances worked perfectly. There is a gas station like 5 mins away from the house which is...
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Mountain Views
    • Shared Outdoor Pool...
    • Waterfront
    • Washer
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Right on a mountain stream, this two-bedroom cabin is very private. No other cabins or homes can be seen. Two double beds make this very accommodating for four. The full kitchen with stove, refrigerator, microwave, coffeemaker, toaster, dishes, pots & pans, and silverware has everything you need... View all property information
    Location Information
    Wintergreen, Virginia 22952
    1 / 10
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    You'll be delighted with this fully furnished mountain home, located just two miles from the Blue Ridge Parkway, and one mile from Sherando Lake. With all the comforts of home, you'll be able to enjoy the outdoors without roughing it! Spend the day hiking on mountains trails, driving on the Blue... View all property information
    Location Information
    Wintergreen, Virginia 22952
    1 / 11
    4.5 of 5 stars (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Grill
    • Internet Access
    • Central Heating
    • Washer
    • Shared Outdoor Pool...
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Nestled in the heart of Wintergreen, a year round resort, this cozy chalet home is a brief walk to the Mountain Inn, ski slopes, restaurants, shops, and market. The house is conveniently located on a private, wooded lot and offers a view of the mountain ranges during the winter months. On warm... View all property information
    Location Information
    Wintergreen, Virginia 22958
    4 of 5 stars Reviewed 15 October 2014
    We stayed there with our friends. The location is perfect, just a walking distance to all attractions. The house was comfy with good size rooms.
    4 of 5 stars Reviewed 21 August 2014
    Spent two nights at this chalet in July, 2014 with my wife, my daughter and her family. There were seven of us and the chalet easily provided the comforts needed for this size...
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    1 / 19
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Patio
    • Shared Outdoor Pool...
    • Air Conditioning
    • Mountain Views
    • Skiing: Property Is...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    We invite you to stay in our newly renovated golf-front condo, right in the heart of the Devils Knob area of Wintergreen Resort. Relax in the private, cozy cottage feel of our condo while having access to the shuttle just outside the door. The Wintergarden Spa and the Nature Foundation are just... View all property information
    Location Information
    Wintergreen, Virginia 22967
    4 of 5 stars Reviewed 9 March 2016
    We loved staying here. Most everything we needed was supplied--even coffee and basic toiletries! The bedrooms were very nice. Full washer and dryer. We plan to stay here again...
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    1 / 37
    5 of 5 stars (6) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Skiing: Property Is...
    • Hot Tub
    • Shared Indoor Pool
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Come play on the mountain! The best location In the heart of Wintergreen Resort. Private but close to everything. You'll be right beside the pool, spa and the mountaintop golf course. All Resort PASSES cover all our guests for Aquatics and Fitness Center right next door with its beautiful indoor... View all property information
    Location Information
    Wintergreen, Virginia 22958
    4 of 5 stars Reviewed 10 December 2015
    I stayed at this condo with my husband, daughter, and friends for a wedding. The location is great and near different attractions. The condo was clean and the owners had labels on...
    5 of 5 stars Reviewed 24 June 2014
    Our family of 6 plus a small child had a fun, relaxing week at this condo. The owner was very helpful and responsive during the planning period. We found the condo to be...
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Hot Tub
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Have a truly special stay at this extraordinary 2-bedroom, 2-bathroom condo with room to comfortably accommodate 6 guests. Once you witness the serene sunset vistas overlooking the valley and mountain, you will never want to leave! Upon arrival, you’ll find that the adjacent free off-street... View all property information
    Location Information
    Wintergreen, Virginia 22958
    1 / 5
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Wintergreen Retreat is a vacation rental home within the Wintergreen Resort in Virginia, set among the beautiful Blue Ridge Mountains. This brand new charming mountain getaway is nestled on Wintergreen Mountain, just a few hundred yards from gorgeous scenic overlooks – and the perfect retreat... View all property information
    Location Information
    Wintergreen, Virginia 22958
    1 / 9
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Washer
    • DVD Player
    • Satellite TV
    • Central Heating
    • Secure Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful 5 bedroom, 2 1/2 bath home located in the Blue Ridge Mountains at Wintergreen Resort, Va.We are a four season community, with golf, tennis, swimming, boating, hiking (Appalachian Trail), skiing, ice skating, tubing, horseback riding, wine tasting, and more, located on our near our... View all property information
    Location Information
    Wintergreen, Virginia 23831
    1 / 14
    5 of 5 stars (24) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    **BRAND-NEW KITCHEN & UPDATED BATHROOMS** Welcome to 'Point of View'! Enjoy the beautiful year-round views from our cozy mountain home located directly on the Tyro ski slope. This is a true four-season get-away. In the winter, step out the door, put on your skis and head down the mountain. If... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 stars Reviewed 20 June 2016
    Just had a midweek stay at Point of View at Wintergreen. We used it as a base for exploring the gazillion wineries in the area! The house is well furnished, comfy. Has all the...
    5 of 5 stars Reviewed 18 February 2016
    The location of this rental is fantastic. Ski in/Ski out! great layout, clean and everything we needed. Owners were a pleasure to work with. We have staying in many rentals at...
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    1 / 13
    5 of 5 stars (5) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Sauna
    • Satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    August 22nd week still available. Book now for Fall/Winter. Luxury House is right on Mountain Golf Course. We have the Wintergreen Resort membership so you have access to resort facilities that are closed to the public! 3500+sq ft Gorgeous/Custom Built House *** Two Master Bedroom/Bath Suites... View all property information
    Location Information
    Wintergreen, Virginia 22957
    5 of 5 stars Reviewed 25 June 2014
    I recently rented this home for a bachelorette weekend for a friend who is more the outdoors type then the Vegas type. It was close to our home in Northern Virginia ~3 hours away...
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